Cunt-Boy Ash
by sinfulnature1123
Summary: I'm kinda known for doing futa stories, so I thought I'd try the reverse. plotless, pointless, smut. Enjoy!
1. Chapter 1

**Alrighty, let's see if this works. It may go horribly, but I'm willing to give it a try if you are. Keep in mind, this is my first attempt at writing a C-boy story, so please hold off on the flames until at least the second or third chapter, as this is just the nice little intro to the concept chapter. It can't be too different from writing futas right? (and he was never heard from again.)**

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Ash had been traveling with Misty for a few days, and they were almost to Pewter City. Misty was kind of annoying, but Ash figured she kinda had the right to be; seeing as in the last three days Ash and Pikachu had destroyed her bike, the center they'd gone to, and caused Misty to be attacked by a swarm of bug types (really it was just a few Caterpi and Weedle, but Misty refused to refer it as anything less than a swarm).

Regardless, Ash was glad for the company on his journey, even if she was a little grouchy. However, after three days, Ash realized the...problem with having a traveling companion: with someone else always around, there was pretty much no time that Ash could have...'to himself', so to speak.

This was fine at first, but after three full days, Ash was getting more and more agitated without any way of relieving the stress. So eventually he just said screw it, waiting up in his tent at night for about an hour after he and Misty had both gone to sleep to make sure Misty wouldn't hear, and decided to try and get off as quickly and quietly as possible.

What Ash hadn't been accounting for was Misty being an extremely light sleeper; a skill she'd honed to avoid being messed with at home with three older sisters. So the moment Ash moaned, even as quiet as it was, Misty snapped awake in her tent.

At first she wasn't certain what had woken her up, then she heard Ash's soft, nearly inaudible moaning. Naturally, her first reaction was one of disgust, 'Ugh, why can't guys go more than two hours without assaulting themselves?' She thought.

But the more she thought about it, she realized that she and Ash had been traveling together for awhile, and he couldn't have been touching himself for all that time. She supposed it was only natural that he wanted to take the edge off, but that didn't make it any less rude for him to do it so close to her tent. Misty then grinned mischievously as she got an idea.

'Well, there's no harm in embarrassing him a little.' Misty thought, getting up from her tent and getting closer to Ash's. Her plan had been to walk across his tent a few times so the noise and sight of her shadow would make him realize she was up and scare him into thinking he'd been found out. This plan, however, was short sighted. When she walked across his tent, Misty realized that he was going at himself so hard that he didn't even notice her.

This led to two thoughts for Misty. One being that Ash was amazing at keeping himself quiet under pressure, the second being that Ash would most likely scream if he saw that Misty had caught him jerking off. That, she thought, was too rich to pass up.

So, with this in mind, Misty poked her head inside Ash's tent. "Hey Ash." She said simply, knowing it wouldn't take much to make him jump out of his skin. Well, Misty had been half right. Ash did in fact cry out in surprise and fear at being caught, but he was not jerking off. He didn't seem to have the right parts for suck an activity. No, Misty was shocked to find that she'd caught Ash with four fingers knuckle deep in his soaking wet pussy.

"What the fuck!?" Misty questioned in shock. Ash nearly fainted, then nearly burst into tears, and scrambled to cover himself up. It took Misty's mind a few moment to work through what she was seeing. 'Ash is a girl? No...his voice and body are clearly male...and why would he pretend to be a guy if he wasn't anyway? But then how...'

The realization, and with it, the reason for Ash's now apparent fear of Misty, dawned on her at the same time.

Ash was a cunt-boy.

C-boys weren't exactly the most popular thing in the world. The pokemon world had equal rights for gender and sexuality, but C-boys and futas were another story; a much, much less fun one. They weren't considered a gender, or even part of the human race. They were declared to be something like mutant freaks, and even though everyone with a brain knew that this wasn't true, they still acted like it was for fear of being persecuted as well.

Misty had always hated the way people treated C-boys and futas...hated the way people like Ash were treated...

Suddenly Misty felt horrible. Ash wasn't cowering because he was embarrassed, he was afraid Misty was going to hurt him or at the very least call an Officer Jenny on him. Misty decided right then and there that she'd make it up to him, and crawled into the tent with him. Misty pulled the blanket off of him, and Ash immediately covered himself with his hands.

"I-I'm sorry, please don't hurt me!" Ash pleaded, Misty hushing him, "I'm not going to hurt you." She promised, taking Ash's hands and moving them aside. Ash hadn't quite finished before Misty interrupted, and his pussy was still slick was juices. Feeling a rush from seeing it, and wanting to make amends with Ash, Misty leaned forward, cautiously dragging her tongue along Ash's slit.

A shiver went through Ash's entire body, making him moan aloud at the unexpected pleasure. Misty found she rather enjoyed the sound of Ash's moaning when it wasn't being restrained; almost as much as she enjoyed the new taste she'd discovered.

Misty had done things with girls before, it was par for the course for a former gym leader; especially with the way she'd acted back then, but Ash's pussy tasted so much different from any girl Misty had been with. It wasn't that it was immediately better, just so truly different from what Misty was used to. Somehow, she felt, that made things even better.

Misty kept going, her tongue beginning to move faster and faster as Ash's pussy got even wetter in response. When Misty was certain Ash was ready, she pushed her tongue inside and began eating him out.

Ash moaned louder, instinctively placing his hand on Misty's head to push her deeper. He'd never been eaten out before, and it was quite an experience for him;l especially with him already being sensitive from playing with himself earlier.

Misty let Ash push her deeper, as she was trying to get her tongue in deeper as well; holding Ash's hips and pulling them closer as her tongue scraped along his inner walls, searching out and and all weak points that made Ash moan even more.

Before too long Ash noticed that Misty was getting horny herself, as it was evident from the growing wetness showing on her bottoms.; as they were meant for night time and were much thinner than normal clothes. Not wanting Misty to be left out or think he was selfish, Ash reached over, carefully hooking his fingers into Misty's bottoms and slipping them down her legs. Once that was done, Ash began shifting Mist's position until they had formed a sixty-nine with Misty on top.

Ash didn't have much experience with his tongue, but for blatantly obvious reasons, he was better at working her pussy with his fingers than any guy Misty had been with, and it didn't take long for him to bring Misty to and passed his point of pleasure. Once Ash had managed to find a few of Misty's more sensitive areas, he was actually able to make her cum before he did.

Granted, only by a few seconds. Once Misty was aware that Ash also had a clit, he was bound to not have long left. It only took a few moments of Misty sucking his delicate nub to make him cry out in bliss, soaking her face in seconds.

The two stayed like that for a few moments, panting, and contemplating what this meant for their travels. If nothing else, they were definitely going to be getting along much, much better from here on out.


	2. Chapter 2

Ash and Misty had been traveling together for a few weeks, and were now enjoying each others company. Problem was, they were now unable to _meet up_ after dark as much as they wanted to, do to their new traveling companion.

Ash and Misty were glad to have Brock along, as he was nice, smart, knew a lot about pokemon and how to raise them, and was an amazing cook. But as happy as they were to have him traveling with them, there was still the issue of his constant presence leaving them without time to themselves to have some more fun.

More than once they'd tried to get away with doing stuff at night when they assumed Brock must've gone to sleep, but he always woke right when they were getting started. It was getting to them both, but Ash was taking it harder.

He'd only just started having sex, having kept to himself for so long out of fear of people finding out he was a C-boy and calling him a freak, and he was by no means ready to stop so suddenly. The pressure was building up just as it always had before, only now he no longer had the benefit of not knowing how good it actually felt.

So, left with few to no options, as there was no unsuspicious way for him and Misty to both disappear for an hour or so then reappear with grins and disheveled clothing, Ash excused himself one night and booked it as far from his traveling companions as he could without getting lost. Once he was certain there was nothing in the area to see him, Ash sat down, removed his pants, and began 'taking matters into his own hands', for rather, taking his own hands into himself.

He'd thought about bringing Misty with him, but again, it would be far too suspicious for them to both vanish then reappear later at the same time, so Ash was on his own for this one.

He kept Misty in his mind though, the thoughts of him and his orange haired lover going at it getting him wet quickly. He began working his pussy over with his fingers as he thought about the time Misty decided to use a strap-on, biting his lip to keep himself quiet.

He had been worried about Misty using the toy when she first brought it out, his male instincts immediately telling him it would end badly if he allowed Misty to use the fake cock on him, regardless of his having a cunt for it. But he hadn't been able to refuse Misty, and besides, it wasn't as though he hadn't thought about using dildos before; he just...never had. Too afraid he figured, and even more so when he saw the size of the toy Misty wanted to fuck him with.

By the time they were finished, Ash was suggesting that Misty buy one a few sizes bigger. He hadn't been expecting it to feel so good, but then again, it was kinda what he was build for from the waist down.

Misty was actually surprised by how well Ash had taken to it, and had started planning all sorts of ways to use the toy, and many others as they managed to buy them.

Ash wished Misty was with him now, using the two sided dildo she told him about. He hated that he was stuck with his fingers again, but the thought that sooner or later the group would reach the next town and he and Misty would be able to sneak away to a private room kept him excited as he touched himself, moaning softly as he was unable to stop himself from making noise completely.

What he didn't know, however, was that Brock had gone off to get Ash for dinner. Misty would've stopped him, but was unaware of Ash's plan to get some relief, and was using the time while Brock was out searching to _de-stress_ as well.

It didn't take Brock long to clear the distance between the camp the group had set up and Ash, Ash hadn't made it nearly as far as he thought he had, and from there he was able to hear the moaning. At first, he naturally assumed it was a pokemon. Being well aware of the fact that pokemon were the only other creatures besides humans that self-pleasured and not exactly the best with people, this was Brock's first conclusion.

He realized what he was actually hearing when he got close enough to see and hear Ash clearly. His eyes widened when he saw the position Ash was in; his pants removed and caught around one foot, legs spread as wide as he could get them, both hands between his legs to pump into his wet pussy with as much force as possible, and face contorted in pleasure.

Brock was a nice guy, and had never approved of the policies against people like Ash, but he'd also never expected to see one; let alone catch one masturbating. What was even more confusing to Brock was him not being able to look away.

It wasn't long before Ash opened his eyes and saw Brock standing there. He immediately froze, his rising climax stopping dead and fading away as panic rose in him. His first thought was to run and hide, but then re remembered Misty, how she'd told him he wasn't a freak. He remembered how nice Brock was, how kind he was.

Not to mention the large bulge in his pants as he watched Ash. Suddenly, a way to fix Ash and Misty's problem became clear.

Ash smiled, beckoning Brock closer. "You just gonna stand there~?" Ash asked with a seductive grin. Brock's eyes widened even more, and his jaw dropped. Ash got up, walking over to a nearby tree and bracing his hands against it, his ass and still wet pussy now facing Brock as Ash wiggled his hips enticingly.

"A-Ash, what are.." Brock trailed off, his eyes drawn to the sight before him. "Don't think about it," Ash said, reaching between his legs to spread his pussy, "Just have some fun~"

Brock was well known for losing it around pretty girls. Now it seemed arousal of any kind had a similar effect. Brock stepped forward, walking over to Ash. "A-are you sure?" Brock asked, slightly nervous. Ash smiled back at Brock, moaning softly as he slipped a finger inside himself.

That was all Brock needed. He dropped his pants quickly, his already solid rod springing free. Ash's eyes widened now when they saw the size, and as Brock grabbed his hips, thrusting into his tight pussy hard, Ash realized he was about to learn why Brock rock the rock type gym leader.

It didn't do much for Ash to hold the tree, as after a few minutes, his entire torso was being pressed into it by the force of Brock's eight inch rod, significantly bigger than the toy, ramming into him at full force. It kinda hurt, but that also kinda made it better. Brock couldn't have slowed down if he wanted to; Ash's pussy was so tight, felt so good, and it'd been so long his Brock actually got any action, he couldn't stop now.

"H-harder!" Ash finally managed to cry out as he came, his slit clenching around Brock tight as he did. Brock didn't need to be told twice. He moved one hand to Ash's shoulder to pull him back even more as he hammered into Ash's pussy from behind. Soon Brock decided he wanted more, and pulled out of him just long enough to turn the C-boy around, lift him slightly, and thrust into him again.

Like this, Ash's back was pressed against the tree, and Brock was able to force his cock even deeper into him. Ash was practically screaming by this point, his legs locking around Brock like a vice. Brock's face was strained in concentration, moving his hips as hard and fast as he could without injuring himself in the desperate need to cum, a goal he accomplished shortly after Ash's second orgasm.

The two fell to the ground, Ash on top of Brock, enjoying the shockingly nice feeling of cum filling his pussy. C-boys couldn't get pregnant, so it was safe. As they laid there panting, Ash grinned, excited to have Misty join them next time.


	3. Chapter 3

Ash could see that May was nervous. She had every right to be of course, this was her first big contest after all. But her being tense and wound up would do her no favors.

"I know," May said with a sigh when Ash brought up the issue, "I just can't stop thinking about what might happen, what if I mess everything up? What if my Pokemon stop trusting me because of it?"

May was clearly overreacting, even she could see that much, but her mind had run off and there was almost nothing that could reign her back in.

Key word of the sentence: almost.

Ash grinned mischievously, getting behind May. May squeaked when Ash reached around her body and began groping her chest, kissing her neck gently. This wasn't the first time they'd done things together. May had caught Ash with Brock, learned he was a C-boy, and she'd been a part of the fun ever since.

May moaned softly, squirming under Ash's touch. "N-now? Really?" May questioned through her moans, not making any attempt to pull away or move Ash's hands. "You're way too stressed out. If you don't relax, you're only going to make things worse." Ash told her, nibbling on her ear the way he'd learned drove her wild, "Plus I'm horny, so it all works out."

May chuckled at this, but couldn't fault his logic. Or rather, didn't really feel like trying to. They had about an hour until May needed to get going, and her dressing room was locked from the inside, so they were good to go.

Ash pushed his hands underneath May's shirt, feeling and massaging her chest. May's breasts weren't as big as Misty's, though Ash was not even remotely dumb enough to point that out, but they felt just as good to him. Plus May's gently, soft moans riled him up much more than Misty's.

Ash began sucking on May's neck, almost certain to leave a mark, as he let one hand trail down from her chest along her body, pausing between her legs. May shivered in anticipation, but Ash went several moments without making any motion to touch her. Right as May began to ask him why he'd stopped, Ash pushed his hand inside her shorts and pinched her clit hard, making her yelp in surprise and pleasure.

Another perk of having May as a partner as well: Ash could finally try out being more dominant rather than always being the default submissive like he was with Brock and Misty. He had to admit, he enjoyed it quite a lot.

Especially when an opportunity to tease May presented itself. Case and point, Ash continued to abuse May's clit, but made no attempt to finger her, and stopped mere moments before May would have cum. May whimpered, squirming against Ash. "You're cruel." She said, fidgeting desperately.

Ash chuckled, "You need to ask nicely~" Ash whispered to her, sending a shiver through May as she felt his breath on her neck. This wasn't the first time Ash had done this, but if May was being honest, she didn't really mind it much. She actually kind of enjoyed it.

"P-please." May managed to get out as Ash began slowly thumbing her clit, "Please fuck me Ash~ Please let me cum~" Ash grinned ear to ear, immediately pushing three fingers inside May, making her gasp in surprise again at the sudden rush of pleasure as Ash began wriggling his digits inside her pussy. "Now say thank you~" Ash instructed, kissing May's face gently as he worked his fingers inside of her.

"Th-tha-ank yo-ah!" May cried out as Ash found a particularly sensitive spot inside May's folds and promptly curled his fingers over it hard to give May as big a jolt of pleasure as possible. "Hm? What was that? I didn't quite catch it~" Ash said deviously, continuing his assault.

May groaned to herself. There wasn't really any way of punishing Ash for this. She enjoyed being submissive too much to just suddenly stop in order to prove a point, and even if she did go dominant, that wouldn't either since Ash liked being submissive to. Truly, there was no way to win. 'Oh well,' She thought to herself as more and more heat built up inside her, 'If you can't win, might as well take it like the bitch you are~'

"I-I said th-thank you." May managed after two more failed attempts at the sentence. Ash smiled, continuing to finger fuck May until her entire body began tensing up. He debated stopping again, as the look of desperation mixed with the whimper as she was denied climax would have been beautiful, but he figured May had earned her orgasm, and let her get off.

May sighed in relief after she came, panting softly for a moment before Ash held his fingers, still drenched in her cum, in front of her face. May didn't even need to ask to know that Ash wanted her to lick his fingers clean. She did so happily, taking his fingers in her mouth and sucking on them until she got all her cum. May didn't mind, she knew her cum tasted great, though not nearly as good as Ash's.

May sat panting for a moment, then got down on her knees, turning around to Ash. Ash smiled as May pulled down his pants and decidedly soaked underwear and licking her lips at the sight of his eager slit.

"You were right, I really did need that. Now how about I return the favor~?" May said, knowing she didn't really need to ask, and not waiting for an answer before she leaned forward, dragging her tongue across his slit a few times to try and repay him for the teasing before pushing her tongue passed his lips slowly.

Ash moaned softly. May always took things slower than Misty or Brock, but Ash soon learned that it was actually just as good as going rough all the way through, possibly even better at times. Not to mention May's tongue was absolute magic. She may use it slow, but she took her time and was able to seek out any and all weak or sensitive spots inside of Ash's delicate pussy and attack them mercilessly.

Even with the door closed, May was certain a few people likely heard Ash when May managed to find a single spot that made him cum instantly, causing him to cry out at the top of his lungs and drench May's face in cum.

May licked her lips clean as she went over to the washing-up area within the dressing room to get herself looking contest ready again. "Thank for that." May said with a smile, most if not all of her anxiety having melted away. Ash smiled, "Any..time.." He panted, already thinking about what he would do for her as a reward when she won her contest.


	4. Chapter 4

**Okay, so yeah, there's a bit of a disconnect between between the times. First Misty, then right to Brock, then all the way to May, and now here we are at an un-specified time after Gary stopped being a dick and started being kind of awesome (that was a stark 180 with little-to no explanation, and frankly it's the only one I've ever seen that I approve of.) So yeah, these are very loose, undetermined times that are the basis for this random collection of only semi-connected chapters. If this is displeasing, then I'm sorry for that, but that sounds more like a you problem. :P**

 **Oh, and a note on the comment concerning the fact that Ash getting knocked up would be hot as hell. 1: Yes, it would, and we all know it. 2: Regardless of that, that isn't how C-boys work. They aren't herms, and are not female in any sense. They are males with female parts, just like futas are just females with male parts and can get pregnant, but can't get someone else pregnant. Confusing I know, even more so when you throw dick-girls into the mix (like futas, but without a pussy and is physically capable of getting someone pregnant and still separate from a herm. Sigh.) 3: If M-preg is your thing, more power to you, but I don't currently have any stories of this kind.**

 **That said, let's get on with the story shall we?**

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Ash had gotten used to spending more time with Gary. Back before they'd been so busy arguing over pretty much nothing, that they'd never actually talked. When they realized this, they decided to fix that and spend the day catching up. Gary told Ash about his studies, Ash told Gary about his travels and his pokemon. Eventually the subject got around to Ash being a C-boy.

Gary looked shocked by this, "Really? Wow..I kinda feel bad. Even if we were always fighting, we were still around each other a lot and I never knew." "Don't feel upset. I kinda went out of my to hide the fact," Ash admitted, "Back then I was really worried about what you would do if you found out."

Gary looked down, and Ash realized that, without meaning to, he'd insulted Gary, saying he was afraid Gary would immediately use the information to hurt or humiliate Ash. "I..I didn't mean it like that Gary." Ash said quickly, not wanting to restart the ongoing feud between them.

Gary looked up, and surprisingly, he didn't look angry, just upset. "I know..but you're right..I was a real jerk back then, and if I ever had found out back then... I probably would have done something really mean and stupid with it. I did a lot of stuff like that back then, and not just to you either. I wish I could make it up to you.."

Ash frowned, then smiled when an idea came to mind. "Well, I can think of a few ways." Ash said with a grin. Gary had never seen that particular kind of grin on Ash before. It seemed...lustful. The thought of Ash being seductive was actually rather amusing to Gary, but never the less when it actually happened, Gary felt heat begin to rise to his face and he looked away on instinct.

"Like..what?" Gary asked, semi-hoping he was wrong about Ash's meaning.

"Well, you're upset that you would've been mean about me being a Cunt boy right?" Ash said, "Well, how about I show you why you shouldn't be mean to C-boys~?" Gary blushed harder at this, and got up from his seat, "Thanks..but really should be going.."

Ash pouted, "Oh come on, do I really weird you out that much?" "No of course not I just.." Gary sighed, "I'm not exactly a very...open person. At least, not with people. never really was. Guess that's why I never really got along with anyone. Even those cheerleaders I used to have on me were being paid to parade around and cheer for me because I never really made any friends."

Ash frowned, "I'm sorry about that, but..I'm your friend now, and I'd like to show you the perks of making friends with a C-boy, if you'd be willing to give it a chance. If not..I can understand why." He said with a slightly sad smile.

Gary bit his lip, then smiled, "You know what..what the hell. **(My personal philosophy ^-^)**

About twenty minutes later, Ash and Gary both collapsed onto the bed in the room at the center they'd rented out for the night. Ash had his arms wrapped playfully around Gary's shoulders as the two kissed heatedly. Gary had slipped his fingers into Ash's pants and begun fingering him, listening to the cute little C-boy moan for him.

Ash wondered how Gary had gotten so good with his fingers if he didn't socialize much, then began wondering if how close he was with his pokemon has something to do with that. He didn't have much time to think on it, as soon they were both frantically removing their clothes, eager to see each other's bodies.

Gary looked in awe of Ash's pussy, currently wet from his touch. Ash was equally shocked by Gary's body, much more fit than he'd expected, though not overly so. His fully erect member was much smaller than Brock, but that was to be expected; at at seven inches, Gary was still on the bigger side.

Ash licked his lips, and pulled Gary on top of him. Soon the two locked together into a sixty-nine, Gary eating out Ash with gusto and Ash returning the favor by sucking Gary off eagerly. Ash had gotten good at blowjobs from practicing on Brock, and decided that while a girl's cum still tasted better, he didn't mind it from a guy.

When they came, Ash shifted over, kissing Gary with a mouthful of his own cum to let him taste it. The kiss turned into a sloppy, cum filled make out session as Ash began to ride Gary. Whether he was aware of it or not, Gary swallowed more of his own cum than Ash did, a thought that turned Ash on wildly and helped him cum in only the first few minutes, his pussy squeezing Gary's cock and bringing him to an early climax as well.

They weren't nearly done though. They had the whole night, and Ash was wondering if he could get Gary to try anal...

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 **Oh, and that tidbit about Gary's cheerleaders being actors that he paid for...yeah, that's actually canon. Just thought I'd put that out there.**


	5. Chapter 5

Ash had been traveling with Dawn for awhile. To avoid the frustrations of going for days or weeks without any fun with Brock while they waited for a moment or two of privacy, Ash instead told Dawn outright that he was a cunt boy and that he and Brock, though not in a relationship, would be hooking on on occasion.

Dawn took it surprisingly well. And was even kind of curious about it. She didn't have a problem with setting up her tent away from Ash and Brock's so that they could have a little private time, but she also never mentioned that she would almost always sneak back over to peek at them. She couldn't help it, she wanted to know what sex with a C-boy was like.

Well, that was the motivation behind her first time spying on them, every time after that was just her wanting something sexy to watch. They would all continue their journey like normal during the day, then at night Dawn would creep out of her tent in her night clothes, move stealthily back to where Brock and Ash had set up their camp, and just enjoy watching them go wild for a few hours at a time.

The first five or so times really had just been out of her own naturally curiosity and fascination, then around the sixth or seventh time watching the two fuck like pokemon in heat, a similar heat started to rise in Dawn herself, and with herself hidden from view, and the sights and sounds of Ash getting his cunt fucked by the Pewter city gym leader so close by, she couldn't help touching herself to it.

The first time she'd tried to ignore it at first, not wanting to be any more of a perv then she already was for watching them to begin with. Then inevitably, she gave in and reached down between her legs, rubbing her slit through her panties gently while she watched. The first time wasn't the best, as Dawn was so worried about being heard or seen that she fled back to her tent before she finished the job and came in privacy. The second time however she got into a more comfortable position on her stomach to watch, her arms underneath her so she could rub herself and a portion of her night gown bunched up and stuffed in her mouth to keep her quiet.

This process worked perfectly, and she continued to do this each time until she decided to experiment. Once she laid in a way where she couldn't see them, but could clearly hear Ash and Brock moaning. She closed her eyes and used the sounds to form a picture in her head to finger herself to. She tried many different positions, each getting a little riskier than the last. During one session Dawn realized that her bare leg had begun hanging over the log she was hiding behind. She started to move it back so she wouldn't be seen..then didn't.

It wasn't so much that Dawn wanted Ash and Brock to know that she'd been watching them, but the fact that they _might_ know, the fact that she _could_ be seen, excited her terribly and helped her cum harder than most all of the times she'd done it before. She didn't quite understand why, but she couldn't argue with the intensity of the climax.

So she kept at it, letting herself get more and more visible as she watched. This reached a boiling point one night with her, fully naked and in full view of both Ash and Brock as she fingered herself, not bothering to stifle her moaning as she watched the two go at it. It was the most intense orgasm she'd had yet...and it also alerted Brock and Ash.

Dawn was just barely managed to get back behind cover before she was seen.

"What was that?" Ash wondered aloud. "It almost sounded like..Dawn." Brock said, Dawn tensing up. Ash laughed, "Yeah, like she'd want to be anywhere near us when we're like this. She always sets up her tent like a mile away."

"True," Brock said, "But who knows. May turned out to be into it. Maybe we should ask Dawn to join us sometime."

Dawn perked up at this. 'Yes, ask me tomorrow night. Ask me!' She thought excitedly. "I don't know," Ash said, "Dawn is really nice. I'd hate to ruin our friendship by asking her to join in and scaring her off." "Yeah, you're probably right." Brock said.

'NO!' Dawn screamed in her head, 'Ask me! ASK ME!'

"Still, it couldn't hurt to act least ask. We'll back off if she isn't interested." Brock said. "Well...okay. We'll ask." Ash agreed.

'Yes!' Dawn cheered in her mind, thinking of all the amazing things she'd do with them tomorrow night. "Hey Dawn, care to join us?" Ash called, facing Dawn's hiding spot.

Dawn's blood froze in her veins. "If not, that's fine; you can still keep just watching if you want." Brock called to her.

Slowly, Dawn stood up from her hiding spot. "H-how did you-" "Oh we've known since day one." Ash chuckled, "You think you're the only one who gets off on being seen?"

Dawn blushed hard at this, opening her mouth to apologize. "Well?" Ash interrupted her with a smirk, "Do you still wanna join us? If not, we don't mind. You're a great audience~"

Ash and Brock went back at it, Brock turning Ash as he rode him so that Dawn had a perfect view of his pussy getting fucked. Dawn sat watching, drooling, and touching herself, for several minutes before she finally worked up the courage to stand and walk over to them, ready to test out everything she'd had planned for tomorrow night.


	6. Chapter 6

**Oh yeah, most of you saw this one coming a mile away didn't you? Well, the more obvious it is, the more it needs to happen eventually.**

* * *

Ash raced through the crowds, dodging between people, jumping over railings, and going three steps at a time to try and catch up to Paul. They'd just had their battle at the Pokemon Sinnoh League tournament. It had been a close battle, one to one odds all around with no real advantages to either of them. After the long battle, be it by that extra ounce of skill or strategy, by luck, or by some other unknown variable, Ash had won the battle by an inch.

And now he was chasing down Paul.

Well, chasing isn't the proper term. Paul wasn't running away from him really, just leaving the League hall. But Ash needed to catch up to him. He just had to. He couldn't let Paul just sink down into his own mind and shutting down like he'd seen him do. There's no telling what would happen to Paul, and Ash didn't want to risk it being something bad.

Eventually, he managed to catch up to the brooding purple haired trainer, needing to stop to catch his breath when he did. "You.. move.. fast." Ash panted, chuckling slightly. "What is it that you want?" Paul asked, his voice more or less devoid of all emotion; save for a hint of agitation.

"See, that's one of your problems." Ash said with a smile, "Not everything someone says or does has to have a reason behind it. Sometimes people can do things because they're fun or because they want to and it isn't hurting anyone. Your head is too locked up in everything needing a purpose, needing a reason."

Paul sighed, and shook his head, "Is that why you chased after me? To list everything I've been doing wrong?" Ash shook his head, "That's another problem: You always assume the worst of everything and everyone around you. Not everything in the world is out to get you you know, you're not _that_ important." Ash said the last part as a joke, but it seemed to strike some kind of cord with Paul.

"But, since you asked, I'm here because I know what you're about to do." Ash said. "You're going to just walk off and start training again." "And that's a bad thing?" Paul questioned.

"Yes actually." Ash said, "Because you're gonna take everything you're feeling, everything you've _been_ feeling, and bury it deep down in the same pit you put everything else. That way you won't have to feel anything and you can pretend you don't feel worse than when it all started. But.."

"But what?" Paul questioned, raising an eyebrow.

"Well, there isn't a whole lot I can do to help you through your issues," Ash said, unaware that he was lying and already had started helping Paul, "But I do know how I can help. I can start by making certain you feel _something,_ and that's the first step."

"And what exactly are you going to try to make me feel?" Paul questioned. Ash gave a cheeky smile, "I'll show you~" He said with a grin, beckoning for Paul to follow him as he headed off. Paul didn't budge an inch for several minutes, then sighed, turning around and walking after Ash.

Ash led him to the room he'd been staying at. He'd asked Brock and Dawn not to come by until later, and they agreed to keep their distance, having a pretty good idea what he was going to try and do. Case and point, Paul opened the door to see Ash on the bed, his clothes discarded across the room. Ash's eyes were closed, and he was moaning softly as he rubbed his own pussy.

Now, Paul was aware that Ash was a cunt boy. But quite frankly, there was a difference between knowing that a Skitty could mate with a Wailord and actually seeing it happen.

"Well~? You just gonna stand out in the door or are you gonna get in here and use me like a stress ball~?" Ash questioned with a slightly challenging grin, knowing that it would work the best on Paul. Sure enough Paul stepped inside and closed the door behind him.

Ash grinned as Paul began removing his clothes and joined Ash on the bed. Paul say anything, and his expression was as unreadable as ever, but the one thing Ash needed to see was in plain view; Paul was hard as a rock and lining up to Ash's slit.

Most people, just on instinct, would start with a kiss before going for it. Paul didn't. Ash noticed this quickly, figuring it was some distance thing. So, to counteract it, Ash pulled Paul's head down, kissing him instead. Paul, oddly enough, actually looked surprised by it; even more so when Ash moved his hips forward, pushing Paul inside him.

Ash moaned softly into the kiss, moving his hips slowly against Paul and parting his lips to give Paul an opening. Paul only hesitated a second before pushing his tongue inside Ash's mouth, letting it mingle with Ash's as he began moving his hips with Ash's.

Soon the two were moving in rhythm, moaning together as they did. They started off slowly, then started picking up the pace. Paul moved his hands to Ash's hips, gripping them tightly as he thrust his cock deeper and deeper with each movement, making him moan louder each time. To Ash's delight, Paul began getting a bit braver, moving his hands along Ash's rear, feeling it's soft skin and beginning to grope and massage it.

Ash moaned louder when Paul began pushing his fingers into his other hole, forcing two, then three, then four fingers inside Ash's ass, pumping them in faster and faster as they kept going. Ash came only a few moments later, his pussy clamping down around Paul's cock hard and forcing him to cum as well.

The two groaned in pleasure together, panting tiredly as their cum mixed and began the process of ruining the bed sheets beneath them. After they'd both regained their energy, Paul got up to leave, only for Ash to grab his arm and pull him back down. "And where do you think you're going?" Ash questioned with a seductive grin, "That round was for you. Now it's my turn~"

* * *

 **Um... sorry if I got a little _too_ caught up in that one. Not sure what happened there.**


	7. Chapter 7

Ash hadn't responded well to Iris' teasing. At first, Iris thought that Ash was just a crybaby that didn't like being called names and being picked on. For Iris, being ever so slightly mean at all times was just second nature by this point, something she did was able to carry out without even thinking about it; sometimes even unaware she was doing until she went over it all in her head again and thought about what she had said and done in the situation.

For her, it was just nature, just how she did things. She very seldom meant anything at all by it, but Ash's response, first to try and ignore her, then to lash out at Iris with as much anger as she gave him, immediately clashed with Iris. His response bothered her on some primal, instinctive level, so she had to pick it up and get meaner and meaner in order to get the intended response from Ash.

Unfortunately, Ash's response to this was to argue and clash even more, trying to get his own intended response out of her. This clashing just kept escalating and escalating, building and building until it inevitably reached a critical breaking point. Iris went on a tirade, ridiculing Ash, his pokemon, and pretty much everything about him. Ash didn't even listen to all of it, after awhile the insults all just blurred together and sounded like a bunch of angry noise.

All Ash was certain of what that Iris punctuated it with, "You don't even deserve to exist!"

Iris was seething. She was primed and ready, already building up to let loose another slew of insults after Ash gave his. But... Ash didn't give his. Ash turned around and ran off. Iris couldn't be sure.. but it looked like he was.. crying.

Iris felt a small pang of guilt, but refused to let herself feel bad for Ash. It was his fault. Why couldn't Ash just take Iris' words in stride and move on? Why did he have to be so determined to win the argument? Iris hadn't even meant to start an argument!

Iris was still seething when Cilan came and sat down next to her. "There's something you need to know." Cilan said calmly. "What? That I need to go apologize? That I took it too far? Save it."

"Ash is a cunt boy." Cilan said.

And just like that, Iris felt terrible. It wasn't a secret to anyone how C-boys and people like them were treated. Isolated, ridiculed, slandered.

Exactly the way Iris had been treated when she first left the village of dragons...

Everyone had just been so ready to believe that Iris was gonna be some weird, crazy dragon lady, that they just started treating her like it before she even did anything; and her massive hair with a pokemon resident inside didn't exactly win her any brownie points with the locals either. Thinking back on it, Iris realized that that had been when Iris first started developing her new 'be slightly mean to everyone' personality. That way at least when stones started flying, Iris could be the one firing the first shot, and when it came time to fight for herself, she'd be ready.

And the realization that that had been why Ash had been so determined to defend himself, so ready to fight, hit Iris like a ton of bricks.

'You don't even deserve to exist...' That's what Iris had said. Only now did she realize the real reason it had upset him so much.

"He's by the stream." Cilan said, Iris rushing off immediately.

Just as Cilan had said, Ash was sitting by the edge of the stream nearby the camp. He wasn't crying or anything, but the pain expression on his face almost made Iris feel worse. She walked over and sat down next him silently.

They just sat there, not talking, for several minutes before Iris said, "Cilan told me...about you." "So?" Ash said.

Iris was confused by this, and Ash could tell. "Cilan told you what I am and now you're upset about how you treated me right?" Ash said, "So what if I wasn't a C-boy? What if I was just a normal guy who you just happened to say all those things to? Would you not be upset about what you said? Would that make it all alright?"

Ash's word hit Iris like a gut punch, and she looked down. "I-I really am sorry Ash, I-" "I know Iris," Ash said, "I know you don't actually think all those things you said, but..why do you have to say them in the first place? I understand wanting to fight back against someone mean, but.. yo u don't need to start fighting if no one is attacking Iris."

"I.." Iris sighed, "You're right... It's just.. I'm always so worried you know? Worried about what will happen if someone catches me off guard." To Iris' surprise, Ash looked up and smiled at her, "Take it from me," He said, "Sometimes..sometimes getting caught off guard is a good thing."

As though to prove his point, Ash leaned forward, pressing his lips gently against Iris'. Iris' eyes widened at the kiss, but when Ash began to move away, she pushed closer, deepening the kiss. Ash began moving his hands along Iris' body, feeling as much of her as he could, and tugging on the hems of her clothes. Seeing Iris was nervous, Ash smiled and reached down, slowly removing his his own clothes, letting her see his pussy.

Iris, even having expected to see it, was still surprised by the sight. Ash's features really were quite feminine when you really looked at him, and Iris could see now that it all fit together perfectly. Iris began removing her own clothes as well, Ash licking his lips as he saw more and more of her mocha skin.

Iris was nearly extremely flat-chested, and from the way she stood, instinctively covering part of her chest with her arms, Ash could tell she was sensitive about it, if only slightly. Iris' legs went for miles, and even without a perfect view, Ash could tell how great her ass was as well. Iris was probably expecting Ash to go straight for her rather luscious rump or comment on her legs, giving praise to her best features, and in any normal situation, he probably would've.

But Iris didn't just need pleasure, she needed a lesson; to learn that people don't automatically focus disliking her worst features or indulging in her best. To show this point, Ash moved his head down and began licking teasingly along Iris' nipples. Her chest was extremely sensitive for being so small, and when he took her nipple in his mouth to suck on it, Iris' entire body froze up in pleasure and left her unable to speak.

Ash made a mental note of this as he moved his hand down between her legs, grinding his palm into her slowly dampening slit. Iris moaned more and more, but refused to just let herself melt under all the pleasure. She moved her hand over, returning the favor and beginning to finger Ash's surprisingly tight pussy.

Ash moaned softly around Iris' nipple, the vibration making her groan more as he kept grinding his palm harder against her pussy. In retaliation, Iris pushed in three more fingers into Ash's pussy, pumping them in fast.

Ash, knowing they'd just end up getting more aggressive with each other like this, decided to change their position. He moved his hand back, and sat with his legs intertwined with Iris'.

Iris didn't understand why at first, until Ash moved his hips forward and began rubbing their pussies together. Both moaned loudly, then grinned wickedly. This way they could both go as rough as they wanted and it wouldn't end up some kind of competition.

Which was good, because by the time they both came, Cilan could hear them all the way back at the camp.


	8. Chapter 8

**For the purposes of my own preferences, I'll be going with the video game version of LT. Surge rather than the anime version, as the anime version was, well, a giant dick; and not in a good way. Also, remember what I said about the timeline being kinda fucked? Yeah...**

* * *

Ash pumped his fist into the air triumphantly. He had just won his third gym battle against LT. Surge. It hadn't been easy, and he and his pokemon had trained for several days in order to manage it, but they'd done it.

Looking over, Ash saw that Surge didn't look at all upset by the loss, and even seemed somewhat proud of it. "Not bad, not bad at all." Surge said, saluting Ash with a smile. Ash smiled to, walking over to Surge. Ash received his badge and prize money for winning the match, shaking Surge's hand proudly.

"You were one of the toughest battles I've had so far." Ash said. Surge nodded, "Same to you. I'll be honest, I'm kind of glad I lost. I love it when a trainer goes all out at one hundred percent right along with their pokemon."

Ash chuckled, "Well how else am I supposed to expect my pokemon to be at their best if I'm not at mine?" Surge grinned wider, "Now that's what I like to hear!"

Ash smiled back, turning to leave the gym. Surge watched him start to leave, then stopped him, "Hey Ash," He said, "How... how would you like to stay for awhile? For, eh, some special training." Surge asked. Ash turned back around to him, smiling. "I was starting to think you wouldn't ask."

Surge felt a little surprised by this statement, and extremely embarrassed. But more than that, he was filled with excitement.

The two didn't linger in the gym long; Surge closing it for the day so he and Ash could have some privacy. They quickly rushed to the bedroom Surge had in the back of the gym, loosing clothing as they went.

It wasn't until they shut the door behind them that Surge realized that Ash was a cunt boy, as they had both stripped down out of all their clothing by that point. He was surprised by this fact, but to Ash's relief, he wasn't grossed out or angry.

"I didn't go to war to protect _most_ people's freedom." Surge said with a smile, stepping forward and pulling Ash into a kiss. Ash let Surge take control, parting his lips and letting Surge's tongue enter and explore his mouth as their hands explored each other's bodies.

Surge loved the feeling of Ash's petite, feminine body as much as Ash loved the feeling of his large, powerful, muscular body. Surge let Ash take control, laying on his back with her straddling him.

Ash could feel how hard Surge was. At ten solid inches, he felt harder than Brock usually did; and that was saying a lot.

Ash smiled, seeing that Surge wanted to show he cared for him by letting him take control. Ash shifted, lining Surge's tip up to his slit and moving down slowly. Ash couldn't just drop down hard like he usually liked to, not without hurting himself and probably Surge to, so he took his time, working Surge's cock inside his warm, eager entrance slowly.

Surge moaned, loving how good Ash's walls felt around his shaft as he worked his way down. "So big~" Ash moaned as he reached the halfway point, rocking his hips so Surge could stir his insides as he took more of his length inside.

Surge took Ash's moaning as inspiration and began moving his hips, thrusting up slowly into Ash. This movement was all Ash needed to reach the base of Surge's member, tensing up around him as he did.

Ash didn't cum yet, forcing himself to hold it back as he began bucking his hips against Surge. Surge grunted, holding Ash's hips and beginning to move them faster as he picked up the pace.

Ash could handle much more, and the dam burst soon as Surge started taking control again. Ash cried out loudly as he came, his pussy squeezing around Surge's rod as his juices ran down it.

Ash panted, then grinned, "I came and you didn't? Well that isn't fair~" Ash got off Surge's cock, getting on his fours on the bed. He raised his hips up for Surge and lowered his head to the sheets, wiggling his hips eagerly, "don't hold back~"

Not ever Surge, a former solder of the Kanto Army could resist that kind of temptation. Surge got behind Ash, lining up and thrusting into his wet cunt with a groan of pleasure. Surge always felt better when he wasn't holding back, and Ash loved it when his opponents gave it there all.

Ash gripped the bed sheets hard, groaning into them. At first Surge was worried he was hurting Ash, until Ash started moving his hips faster to match Surge's speed, moaning, "Harder~"

Surge grinned, picking up the pace and ramming his stiff rod harder into Ash, making them both moan louder as the bed began to shake from their movements. Ash came again before too long, his slit once again clamping down around Surge's length as he did. This time though, the extra tightness from Ash's climax was enough to push Surge over the edge into his own.

Surge was thankful c-boys couldn't actually get pregnant, because he couldn't have pulled out if he wanted to, releasing a flood of white hot seed into him, making Ash shudder in delight.

Ash moved back, turning so he was on his chest on the bed, level with Surge's still hard member. "You only came once. I'll have to fix that." Ash said, leaning forward and taking Surge's shaft inside his mouth and beginning to suck him off. Surge moaned, wondering how Ash had gotten so good with his mouth.

Ash kept coming up with excuses to keep going all night long, not that they really needed any. By morning, both of their legs were practically numb. Which was fine; they spent the entire next day in bed anyway.


	9. Chapter 9

Clemont always got a kick out of watching Ash and Serena battle. The two were like mirror images of each other. They matched in nearly every way possible. The funny thing was they didn't seem to notice it, and were always surprised by how they were able to keep up with each other, especially when it came to pokemon battles. By the end of them, both of them were riding massive adrenaline rushes, to the point that Clemont was surprised they didn't strip down and start fucking then and there.

What he wasn't aware of, though it wouldn't have surprised him if he had known, was that by the end of a battle, both of them _did_ want to start fucking right then and there. They only didn't out of a shared fear that the other would reject them; Ash believing Serena might judge him for his true gender and Serena believing that if Ash really did have any attraction to her, he would've shown it by now.

It became a viscous cycle of both of them _almost_ making a move but neither quite working up the nerve to do it. Finally, having caught on to what was happening, Clemont decided to try his hand at playing match maker, and hoped the idea wouldn't blow up in his face like most of his devices seemed to do literally on a quite regular basis.

It was a simple plan, one that had been done before and would be done again, but given the circumstances, he figured it would work well here. He waited until right after Ash and Serena had a battle, and Ash was in the shower. He went to Serena, telling her that the woman's shower was out of order, but that she could use the guy's wash room instead.

"The place was empty a few minutes ago, it should still be now." Clemont lied through his teeth. Serena thanked him, and went up to the washroom. Clemont had put up a small noise canceler he'd built awhile back, so even with Ash showering, Serena couldn't hear any noise coming from the bathroom. Hearing it silent, she assumed Clemont was right about it being empty, and walked right in...

Her eyes widened when she was met with a direct view of Ash in the shower, drenched in the steamy water and covered in soap. Clemont had known that Ash was a cunt boy, and now, so did Serena.

Ash yelped in surprise when he realized Serena was there, and actually slipped up; falling to the ground and landing on his ass. Serena, worried he'd been hurt, hurried over. "Are you okay?" She asked him quickly.

"Yeah, I'm okay..." Ash said, looking up at Serena with a massive blush on his face. He looked down in embarrassment, crossing his legs to hide what Serena had already by then.

Serena bit her lip, unsure of what to say. "Well, that certainly explains a few things." Serena finally managed to say. "I..I'm sorry i didn't tell you.." Ash said, still looking down. "Are you kidding? I wouldn't have said anything either." Serena said, "I mean, I've heard what they say about c-boys in other regions."

"Yeah, I was just so worried that...in other regions?" Ash asked, confused. Serena nodded, "Kalos has never been against C-boys or futas. The stereotyping just never happened here. We've even got a futa in the elite four."

"What? Really?!" This was news to Ash. He's thought the gender hate was across the map, he never knew there were safe zones.

Serena nodded, then moved her face closer, "So, tell me something: if you'd known I didn't care what gender you were, would you have made a move by now~?" Now that she saw a chance that Ash might actually want her as much as she wanted him, she was taking it; for better or worse.

Better, is turned out, when Ash closed the short distance between his and Serena's faces and pressed their lips together. It was just a small, lip deep kiss, until Serena took more control, pushing her tongue into Ash's mouth. Ash was more than happy to submit, letting her explore his mouth and take full control of the kiss as she instinctively pressed him onto his back.

They stayed like that, making out heatedly on the shower floor for several minutes before separating; and even when the kiss did finally break it was only so Serena could undress herself to match Ash. Ash couldn't help but stare as Serena removed her clothes, showing off her soft, firm C-cups and slightly small rear. She returned to Ash, getting down and pushing her head between his legs.

Ash had been with a few people of both genders by this point, and was fairly confident in his ability and pleasure threshold. All of this melted away the moment he felt Serena's tongue enter his slick pussy. If not for Clemont's noice canceler, the whole center would've heard Ash's shrieking as Serena explored his insides with her highly skilled tongue. it was like nothing Ash had felt before!

Ash came in only a few minutes, crying out Serena's name. Ash didn't know how Serena got so good, but he was now determined to prove he was good to, and had her shift so he could return the favor. Ash plunged his tongue into Serena's wet pussy eagerly, reaching around and grabbing her ass to pull her more against him. Serena moaned loudly from Ash's tongue, but Ash could tell she was more skilled then he was. To compensate. Ash moved one finger over, prodding the entrance of Serena's other hole.

The blonde trainer squeaked in surprise, moaning louder as Ash pushed one finger inside her tight anus while he ate her out roughly. Serena held on for another five minutes before cumming upon Ash's adding a second finger.

Ash licked Serena's deliciously sweet juices off his face, grinning at her. In that moment they both shared two of the exact same thoughts. The first was, 'we're not even close to done,' and the second was, 'why the hell haven't we been fucking this whole time!?'


	10. Chapter 10

Ash loved spending time with Richie. He wasn't sure what it was, but no matter where they were or what they were doing, they always seemed to end up having fun so long as they were doing it together. By this point they were battling together, training together, shopping, eating, and exploring together. They'd even just go out into whatever town happened to be nearby and just do things together. Didn't matter what, food, movie, whatever happened to be around.

"So basically, you're dating him." Misty commented with a smirk. Ash blushed hard at this comment, "W-what? We aren't dating." Misty rolled her eyes, "Hate to be the one to burst your little bubble, but yeah, you really are. There's nothing wrong with it Ash, I don't mind. I actually think it's kinda cute." Misty added with a wink to tease Ash. She loved embarrassing her friend and part time partner in bed.

Ash blushed harder. "Oh please, Richie wouldn't think of me like that." Ash said, head down. "Oh, so you want to be dating him then?" Misty teased. "Oh would you quit it?" Ash said.

"Nope." Misty said, "Listen, if you want to know if Richie wants to be dating you to, which just for the record, he totally does you clueless goof, then just ask him on one. You already go out with him every night, just officially call it a date and see what happens. Worst comes to worst, he gets weirded out and you say, 'JK bro', or whatever guys say."

Ash opened his mouth, then realized that that could actually work. "Thanks Misty." He said with a smile. "No problem." Misty said, "I'll even leave the camp for the night so you two can come back here when you start fucking." "Misty!"

* * *

Ash was relieved to see that Misty hadn't just been joking, and really had cleared out of the camp for the night. Richie hadn't even questioned him calling their trip into town a date, and even seemed excited about it.

"I'm glad you finally pointed it out," Richie had said, "I was so terrified to try to do it."

Ash was stunned by this, and made a mental note to eat Misty's pussy raw later on to thank her. At the moment, they'd just returned to the camp, Misty nowhere to be seen. Richie looked so cute in the firelight, Ash couldn't help himself. He leaned forward and kissed him.

To his relief, Richie kissed him back; even parting his lips to allow Ash's tongue access to his mouth. Ash eagerly explored Richie's warm mouth as the two began feeling each other up. The kiss lasted several minutes, which resulted in a thin saliva string connecting their mouths for a few seconds after they moved back.

Clothes were gone in seconds. Richie already knew Ash was a cunt boy, so there was no surprise there, save for maybe how hot it really was. Ash however, was in for a shock when he saw Richie's ass as realized just how great it looked. Soft, round, tight; fuckable in every way.

Ash leaned forward, kissing the tip of Richie's slowly growing member. He wanted Richie's ass, but he knew he'd have to earn it first. At full length, Richie was only about five inches; easily deep-throated. Ash took all five inches into his mouth and throat with no difficulty, sucking gently as he bobbed his head. Ash figured Richie didn't have much experience with oral, because he came in only a minute's time. Not that Ash minded; Richie's cum was warm, delicious, and felt so good sliding down his throat.

Richie didn't even get a word in before Ash leaned forward, circling Richie's tight, puckered entrance with his tongue. His face burned red, "Th-there?" He questioned. Ash move his head back and looked up at Richie, "Do you not want me to?" He asked. Richie couldn't bring himself to honestly say no, and Ash continued. He pushed his tongue in slowly, scraping it along Richie's walls.

Richie moaned softly, making Ash move his hands between his legs and start fingering himself as he listened and probed his tongue deeper and deeper into Richie's anus. Richie's cock got fully hard again from this, but before he could cum, Ash pulled his tongue back out, making Richie whine at being denied his climax.

"You have two options." Ash said, "I can get on my hands and knees and let you fuck me, or you can let me go get a special toy to fuck your cute little ass even deeper~"

Richie's silence after this question was expected, but so was his inevitable answer. Ash's toy was double sided, and he pushed the first six inches into himself slowly as he approached Richie. Richie opened his legs for Ash, spreading them wide as Ash lined up the tip of the toy to his puckered; already lubricated with Ash's saliva.

Ash pushed the toy in gently, his moan coming at the same moment as Richie's. Ask worked the toy into both of their holes slowly, soon hilting them in on both sides. They took a moment to adjust to the length inside, then began moving their hips together. It was out of sync for a moment or two, but soon Richie and Ash were pumping their hips together in rhythm; letting the toy fuck both of them deeper and deeper as they did.

They held onto each other's shoulders as they bucked their hips together, moaning to each other as they went, feeling the toy go deeper and listening to the pleasured cries of their partner. It was intoxicating.

They came together, and came hard; Ash leaving a puddle of fluid under them and Richie coating Ash's stomach as well as his own in hot cum. They collapsed panting in a warm, happy, tired heap, struggling for a moment to crawl into the tent and remove the toy before they dropped into the spot they'd be sleeping together for the night, limbs entangled peacefully as they thought about what to do on their next date.


	11. Chapter 11

**Those of you who haven't seen Pokemon Diamond and Pearl Battle Dimensions, specifically the summer academy arc with a certain female character who may or may not be my all time favorite ship for Ash in the entire animated series, stop reading this, go watch, and come back.**

 **Are you back? Good. Time for the C-boy version of my personal pokemon OTP! ^-^**

* * *

Ash and Angie couldn't have had a more tsundere relationship if they'd tried to; which they may have actually done a few times. Even once they'd started showing their feelings for each other more directly and admitted how much they liked each other, they still clashed every other day. The clashing never seemed hostile, even if it did get intensely aggressive when it didn't need to.

Dawn and Brock theorized that they just needed to start fucking and get the tension out, but they knew that saying it to them would invoke hostility from both of them, so they decided to sit back and let it take it's course.

It took about two weeks for things to reach a particular boiling point. Dawn was right about most of Ash and Angie's frustrations stemming from a bit of sexual tension. In fact she wasn't even aware to what extent she was correct. Ash had stopped sleeping with Brock and Dawn for the time being, feeling like it would be cheating on Angie if he did.

As a result, Ash had no outlet except masturbation, and with his sleeping quarters being in such close proximity to several other people who he didn't nearly trust enough to keep his c-boy secret. So even masturbating was off the table. Angie at least could touch herself if to take the edge off.

All the tension came to a head when Angie went to her room and opened the door; her eyes widening in shock.

Synapses began misfiring in Angie's brain as she tried to process everything she was seeing. Ash was laying on her bed, naked save partially for his underwear which was pulled down and was around his left ankle. His legs were spread wide, unintentionally giving Angie a perfect view of his sopping wet pussy, which he was pumping four fingers into roughly with one hand while the other pressed a pair of Angie's panties against his face.

"What the fuck!?"

Ash froze, and all the color drained from his face when he saw Angie staring at him in shock. Ash had had the good sense to admit to being a c-boy to Angie when they started dating, but that hardly explained this situation away.

The awkward was tangible in the air as the two remained silent and motionless for two full moments before Ash spoke, "We're definitely done, aren't we?" Ash asked, hoping he was wrong in this assumption, but almost certain he wasn't.

Angie's mind had been working overtime from the moment she fully comprehended what she was seeing. She took another full minute to respond with shaking her head. This, for a moment, actually worried Ash more than if Angie had just dumped him on the spot; which he was sincerely shocked didn't happen.

Instead, Angie walked in and across the room to her dresser. Without a word to Ash she opened the bottom door and reached in under all the clothes. Ash's eyes widened when he saw what she pulled out.

Ash wasn't sure how he should feel about the strap-on Angie took out. On the one hand, it meant that Angie wasn't nearly as angry as she rightfully could be, and that she was at least partly frustrated like he was. On the other hand, it was easily bigger than any toy or even normal cock he'd ever taken, and Angie had an almost sadistic gleam in her eyes as she began removing her clothes.

"Don't worry, I'm not mad Ash. This is my fault as much as yours." Angie said, pulling her shirt off. She was practically flat, but Ash's nose still bled when he saw her exposed chest and bald pussy. Angie blushed when she saw it, then grinned, putting on her toy as Ash wiped it off his face.

"I've had this toy for awhile, but I've never gotten to use it on anyone." Angie said as she took out a bottle of lube to slick the shaft of the strap-on. "Let's face it, if we don't have a little fun, we might end up killing each other. So," Angie grinned again, "Pick a position."

Ash decided to stay on his back, wanting to see Angie's face for their first got on the bed and lined up the massive toy to Ash's slit. Ash gulped, and Angie smiled, leaning in and giving him a kiss, "Don't worry, I'll be gentle. Until we both get bored of it."

Angie pushed in slowly, only for Ash to wrap his legs around her waist and pull her in faster. "Bored now~" Ash moaned as the large toy stretched out his pussy. Angie grinned, gripping his hips and ramming the toy in hard to hilt it before pulling out to slam back in.

In retrospect, Angie asking Ash to pick a position may have been a bit redundant, as they went through every position they knew between the two of them that night at least twice. By the time the sun had risen, Angie had claimed ownership of all of Ash's holes repeatedly, and both of them felt more exhausted, and more importantly, satisfied, than they had in a long time.

In the days that followed, unlike Dawn's prediction, Ash and Angie actually slashed more often as opposed to less. Now, however, there was no aggression behind it. They treated it like a playful game or inside joke they shared; once even getting worked up from am argument to the point that they had to stop the actual argument to fuck in the nearest bathroom.

Dawn and Brock figured it wasn't a problem. They weren't angry, and they were actually enjoying themselves. They weren't hurting each other. Well, that might not be accurate. Ash walked with a limp almost every other day, and Angie did on the days Ash didn't. Regardless, they always had blissful smiles on their face afterwards.


	12. Chapter 12

Ash wasn't usually a fanboy. His mindset was one for fanboying. He could be impressed by someone famous or a strong trainer, sometimes more easily than he should have been, but still. Ash just wasn't the fanboy type.

This rule did not apply to Bruno.

Ash wasn't sure why, but whenever he saw Bruno, be it on screen or in person, he had to hold back an excited squeal, and usually ended up wet if he kept watching for too long. Maybe it was the muscles, Ash thought, he knew he got turned on from Brock's muscled form. But with Bruno... it was something else.

So needless to say, when Ash came across Bruno training in a rocky valley area, wearing only his shirts as he and his pokemon both worked out, Ash nearly drowned in his own drool. Ash rationalized that he definitely wasn't just spying on a hot guy, he was merely observing a powerful trainer to learn how to better his own pokemon training. He couldn't quite rationalize why he was getting moist between the legs from watching Bruno power lift boulders and chuck them across the valley though.

Regardless, Ash kept watching in delight. He wasn't sure how long he stayed there to watch, it was all a bit of a blur after he started touching himself. It must have been awhile though, because after some time, Bruno recalled his pokemon and went about his own personal training for another ten or twenty minutes before sitting down to rest.

Ash squinted, trying to see what exactly Bruno was doing now, but he couldn't. 'Just learning from a powerful trainer,' Ash reminded himself as he snuck down the valley to get a closer look at Bruno.

As he got closer, Ash started to recognize the motions Bruno was making, but his mind refused to recognize them at first. No way he could be doing that...right? but the closer he got, the clearer it got to Ash that he wasn't just misinterpreting what he was seeing. When Ash got on level ground to Bruno, he was able to see that the elite's pants were pulled down, and his hands were pumping along his cock, which was painfully hard.

Ash's jaw dropped at how big Bruno was. And he though Angie's toy had been big! Ash couldn't begin to guess how big it actually was, but he would have had to place it at around fifteen inches, if he was rounding down. Bruno's cock was so thick he needed to use both of his powerful hands to stroke himself off, and even then he didn't see, to be making much progress with how hard he was.

"I-I can help with that if you want." Ash said, stepping into sight. Bruno didn't seem fazed by Ash's presence, didn't even stop pumping his hands along his length. "You can?" He asked curiously. Ash nodded, forcing himself not to squeal or faint as he approached.

Ash got onto his knees, Bruno moving his hands away and letting Ash grip his turgid cock. Ash was drooling as he kissed Bruno's tip before trailing his tongue along the length while pumping his hands around the base. He kept this up for a few minutes before stepping back, "I don't think I'll be able to fix it like that," Ash said, removing his clothes, "But maybe this'll work~" Ash said, using his fingers to spread his pussy lips as he leaned back against the rock wall.

Bruno licked his lips, going over to Ash. He picked him up and essentially just dropped him down on his cock, making Ash scream out just from the first third of his cock. Ash felt the rocks press painfully against his back as Bruno thrust into him hard as he pulled his hips back to force himself deeper into Ash.

Ash tried to move someway to help Bruno out, but soon realized that Bruno didn't need any help. With his strength and size, Bruno had managed to sink half his length into Ash's pussy within ten minutes. His stomach was extended a bit, and Ash had gotten at least twice as tight from cumming at least three times, but at no point did Bruno ease up. And if Ash was being honest, he didn't want him to. Ash could tell he was going to have marks and bruises on his back for days after this, but at the moment, he didn't care.

Bruno switched the position, taking Ash to the ground. Bruno gripped Ash's legs and pushed them up so they were both over his shoulders while he thrust down into Ash, literally fucking him into the ground. Ash's tongue lulled out of his mouth as he came a fourth time, then a fifth when Bruno finally got to the base and bottomed out inside him.

Ash couldn't remember ever being fucked this roughly before, and he was loving every second of it as Bruno used him like a living onahole. Bruno's eyes were squeezed shut, his teeth clenched, his whole face set with concentration as he hammered into Ash harder and harder, having at some point forgotten there was an actually person there and disregarding any thought of the pain it might cause them if he simple used them like a toy to reach what was bound to be an extremely powerful orgasm.

Thankfully Ash really was enjoying it, and screamed out with his sixth climax only seconds before Bruno practically growled as he went over the edge, finally reaching his destination and releasing a massive flood of cum that Ash could in no way contain. Ash was filled to the brim and then some, the burning hot seed spilling onto the ground as Bruno pulled out, still cumming as he did and coating Ash's legs and hips as well.

Bruno sighed in immense relief. "Thank you very much, that really was a huge help." Bruno wrote down his number and gave to Ash before heading off, leaving a barely conscious and blissfully happy Ash in a puddle of his and Bruno's cum.


	13. Chapter 13

Sabrina had had an interesting few days. She couldn't quite remember the past few..years. Her mind had been in fractures since she was very young, but now, thanks to a silly little Haunter and an overly determined pokemon trainer, she was free from the chains of her own mind. She was lucid, fully aware of the world around her. It was an odd experience, but it was good. Very good.

She couldn't thank Ash enough for it, especially with him constantly denying that he'd done anything at all. "Haunter did all the work," Ash insisted, "All I did was bring him here, for the wrong reason no less." Ash said. Sabrina couldn't help but giggle at this. "I'll still find some way to repay you." Sabrina said, giving Ash a kiss on the cheek, making him blush.

Sabrina knew exactly how she would repay Ash's kindness to her. She had seen what her powers could do when used maliciously, and Ash certainly had as well. So what, she wondered, was she capable of she wanted to do something nice instead?

From the look on Ash's face when he woke up on the lavish bed laying next to her, quite a lot. "Sabrina? How did I get here? Where is here?" Ash asked, looking out at the dimly lit landscape. "It's called the dreamscape." Sabrina said, "it's like another world inside your dreams. I can use my powers to travel to and from this place, and I can even bring others with me in their dreams."

"So...this is a dream?" Ash asked. "Well, sorta," Sabrina said, "It's more like an advanced version of telepathy. Instead of just hearing my voice in my head, you can also see me, and touch me." Sabrina added with a grin, trailing her hand along Ash's leg. "It works wonders for rewarding kind souls~" Sabrina said, snapping her fingers. Instantly her clothes were gone, revealing her large D-cups and smooth body to Ash.

Ash blushed hard at this, "Uh, Sabrina...you should probably know.." "That you're a cunt boy?" Sabrina finished for him. Ash gave her a bewildered look, and Sabrina giggled, "I'm a psychic remember? I've known what you were sporting down there since you first walked into the gym. I'll be honest, it has me quite curious." Sabrina said, her fingers wrapping around the edge of the blanket, "I've been with both men and women, but I've never had a herm, futa, or a c-boy. This should be an exciting night~ especially with this being the dreamscape, where I can do this."

Sabrina snapped again, and her body changed. Not much mind you, just changing her from a woman to a futanari with a good solid seven inches in a matter of seconds. Ash was shocked by all Sabrina could do with her powers, but figured it was to be expected from someone who was turning people to dolls and vice versa a few days ago.

"Now, if you'd rather I be a woman for this, or if you'd rather we not do it at all, let me know now before I get too riled up~" Sabrina said, beginning to pull the blanket down. When Ash didn't object, Sabrina pulled the blanket away, licking her lips at the sight of his pussy.

Sabrina leaned down, placing her head between his legs and beginning to lip his pussy gently. Ash moaned softly, then got louder when Sabrina's tongue got more aggressive. Sabrina had no idea where she'd gotten so much experience with her tongue, most of her memories were still scrambled, but if she had to take a guess, she believed she may have found the reason why the channellers, who were primarily ghost type trainers, were operating in her psychic type gym.

Ash held onto Sabrina's head, his groans of pleasure getting louder as Sabrina used her psychic to rub his clit as well, and even began gently rubbing his puckered rear hole for even more stimulation. Ash's whole body was twitching and squirming from the intense pleasure, and it wasn't long before he cried out, covering Sabrina's face in his juices.

Sabrina licked her lips, "Delicious~" She purred, "Now let's see how you feel~" Sabrina had Ash lay on his side and lift one leg up, which she held up as she thrust her new member into his soaked pussy. Sabrina wasn't sure who moaned louder, Ash at the feeling of being penetrated by her, or herself from the intense, unexpected pleasure around her new appendage. Was this what guys felt like all the time during sex?! No wonder they wanted it so bad!

Sabrina, with her new found understanding of the world, vowed to be a little more considered of men and futas who approached her in need of pleasure, and began bucking her hips against Ash's, pushing her member deeper into him. Sure enough, it only felt better the deeper she got, and Sabrina had to resort to psychically cutting of the pleasure response in order to keep from cumming too soon. This was Ash's reward, not hers.

Luckily she did manage to make Ash cum before too long, just twenty minutes of progressively picking up the speed until the whole of the bed was shaking with every movement later, Ash screamed out Sabrina's name, his pussy clamping down around her cock as he came.

Ash took a few moments to catch his breath, then grinned at Sabrina. Sabrina couldn't feel anything from the waist down with the feeling in her member turned off, and with her having laid down on the bed to rest as well, she didn't notice Ash sucking her off until she reactivated her pleasure perception and all the sensation she'd been blocking rushed forward at once along with the added feeling of Ash's warm, wet lips around her cock.

Ash nearly gagged the cum shot so hard down his throat. It still tasted good though, as he was sure to tell her. Sabrina smiled at this, and decided to make her futa form her new base form for the dreamscape. She'd be visiting Ash, and perhaps even a few other friends, in their sleep for more fun from now on.


	14. Chapter 14

**WARNING: pokephilia. I usually have a 'if you didn't want to see fucked up stuff then why the hell are you on my channel' policy, because putting up warnings like this tends to give away surprises, but after that one little surprise yaoi chapter in the Fox's Harem, people have been getting real fucking bitchy about it.**

* * *

Ash laid down on his bed. It had been a long, long hard journey across six whole regions of the world, and there would likely be just as much left of it to go before he was truly done. So it was nice that he could stop by his mother's house every now and then to just relax for a day before heading back out into unknown adventure. His bed was always soft, his blankets always warm, and night always peaceful.

It did bother him to be without his pokemon for so long, but he still had Pikachu with him. His first pokemon was somewhere down stairs at the moment, likely asleep next to the fire place or TV. This, Ash thought, was the perfect time to work off a little stress before he went to sleep.

He pushed the blankets back and discarded his pajama bottoms. His bed was always soft, perfect for resting his back on, especially when it came to activities like this, Ash struggled to keep his lips sealed and his teeth clenched as he began fingering himself gently, wanting to just get off quickly and go to sleep.

Any chance of that happened instantly died when Ash heard the door open. He could tell it wasn't his mom from the lack of footsteps. He knew he needed to stop before Pikachu saw him doing this, but he was so close, he couldn't just stop like this, it was torture.

He decided to risk it, and kept going for another few seconds to get himself off. His whole body tensed up for a moment before he went still, pretending to be asleep and hoping Pikachu either hadn't seen anything or had seen little enough that, as a pokemon, he wouldn't understand it. Ash often forgot that the majority of pokemon, Pikachu included, are on par with humans in terms of intelligence. The misconception of them being closer to animals came from pokemon being more sensitive to instinct than humans were.

Ash had hoped Pikachu would just wonder back downstairs to go to sleep, but instead he jumped right up onto the bed. Ash swore internally, but figured it wasn't too big of a deal. He'd already gotten off, he was in his soft bed; he could sleep like this. He'd hoped to be able to pull his pants up, but with Pikachu sleeping at the far end of the bed like he always did, there was no harm in it.

Ash didn't realize that Pikachu wasn't going to sleep until he felt the tiny mouse pokemon's tongue brush against his slit. Ash's whole body tensed in surprise and unexpected delight at the contact. Pikachu repeated the motion several times before pushing his tongue inside and beginning to eat Ash out.

"P-Pikachu, what are y-you d.." Ash was cut off by his own moaning at Pikachu's work. He couldn't help it, he was still sensitive from his first climax, and Pikachu's tongue felt amazing inside him, especially when he began using his soft paws to rub Ash's clit.

"P-Pikachu, I-I-ah!" Ash yelped a bit louder than he meant to as he came, soaking Pikachu's face. Pikachu licked his lips, and smiled up at Ash, who was looking down at his pokemon, baffled. "You were waiting for an opportunity like this, weren't you Pikachu?" Ash concluded, his suspicion confirmed by Pikachu nodding in agreement.

Ash had never considered his pokemon wanting to fuck him before. Hell, he'd never thought about his pokemon having sex, It just wasn't one of those things that usually crossed your mind, unless you were completely mad or just plain sick **(Or both, like me!)**.

Ash bit his lip as Pikachu looked up at him. He knew that pokephilia was taboo and what not, but he couldn't quite bring himself to view it as wrong, not after all he'd been through with Pikachu. It was just a little fun, what could honestly be wrong with that?

Ash smiled, "You're pretty good with your tongue Pikachu." Ash commented, Pikachu grinning, an replying with a series of gestures that Ash translated as 'I've practiced on some of the other pokemon we'd traveled with. Celebi tasted the best.'

"Really?" Ash asked, Pikachu nodding. Ash knew his life would be forever changed, because now he lived in a world where the thought, 'my Pikachu is a player' had actually crossed through his mind. "Wow, I never knew you got around with the other pokemon so much. Tell me, do you wanna keep going~?"

Pikachu didn't hesitate to nod, grinning eagerly. He propped his front paws on Ash's stomach, and lined up his member, already fully erect at about four inches; quite large for a Pikachu. Ash moaned softly as Pikachu thrust into him. The difference is size actually turned out to make it better, as Pikachu could be as rough as he wanted without making too much noise and waking Ash's mom.

Ash was surprised by how much he was enjoying himself, and was starting to wonder why he hadn't thought of this sooner. He bucked his hips against Pikachu, taking his entire cock easily. Pikachu came first, but a well timed low voltage jolt from Pikachu's paw through Ash's clit triggered Ash's climax early so he was able to cum only seconds after his pokemon.

The two laid together in the bed, warm and happy under the blankets. His experience with Pikachu got Ash wondering though... did any of his other pokemon wanna fuck him? **(Hint, hint. Finale, next chapter~)**


	15. Chapter 15

**Alrighty everyone, are you ready? Let's finish this off!**

* * *

Ash had decided to take a little break from his journeys to relax and have a little _quality time_ with his pokemon. With a lot of his pokemon either training or just not around, Ash was able to research a little spot in the fields at the ranch where Oak kept all the pokemon in the PC with his Bulbasaur, Snorlax, Charizard, Bayleef, Quilava, Torterra, Infernape, Snivy, and Buizel.

All of them were extremely excited to be seeing their trainer again; but were even more excited when they learned why and Ash stripped out of his clothes. "So," Ash said with a seductive grin, "Who's first~?"

The question was largely redundant, because everyone knew who was going first. Bayleef tackled Ash to the ground immediately, licking his face excitedly. She'd been waiting for this since she was a Chikorita. Ash giggled, catching Bayleef's tongue in his mouth and beginning to make out with her, placing a hand on the back of her head to hold her close as they kissed.

Bayleef moaned softly from the kiss, squealing in glee on this inside at one of her greatest fantasies being realized. Ash reached down between her legs and began rubbing her pussy gently with his fingers. Bayleef moaned more, moving her hips against Ash's hand, moaning more and more at the touch. Ash knew full well that Bayleef wouldn't be able to get off just from his fingers, so he moved his hands back and spread his legs for her.

Bayleef grinned, lowering herself down so her pussy pressed against Ash's as she began to buck her hips against him. Bayleef groaned in pleasure at the contact, using her vines to hold Ash close as she ground herself against her trainer.

"You feel great against me Bayleef~" Ash moaned, holding onto her shoulders. This urged the Bayleef to pick up the pace, wanting to make her trainer feel as good as possible. Ash moaned as he moved his hips against his Bayleef, barely able to keep up with her fast pace as she used all four legs to help grind herself even faster against him.

Ash cried out in pleasure as he came moments later, Bayleef backing up and looking down at him for approval. Ash smiled up at her, "That was great Bayleef~" He praised her, sending a shiver down the grass type's spine. "But you didn't get to cum," Ash added, "I'll fix that~"

Ash leaned forward, pushing his head between her legs and beginning to lick her pussy. Her juices were quite fragrant, like an intoxicating mix of fruit and spices. Ash lost himself in eating out her eager folds, licking deeper and deeper until he was rewarded with a flood of juices as the Bayleef came, her face burning red as she cried out in bliss.

Ash licked his lips, and kissed Bayleef again to let her taste herself before moving back away from her."Who's next~?" Ash asked as Bayleef laid down tiredly. Several pokemon likely would have stepped forward, but Bulbasaur was the fastest; wrapping his vines around Ash's waist and pulling him over. Ash grinned as Bulbasaur used his vines to push Ash down gentle.

Ash leaned forward, gripping Bulbasaur's member and stroking it gentle until he was completely hard. Once he was, Ash leaned forward and began to lick his tip teasingly. In retaliation, Bulbasaur began tracing the tips of his two vines around the edges of Ash's two holes, never entering either.

Ash squirmed from the teasing before finally giving in and taking Bulbasaur's member into his mouth to suck him off. Bulbasaur moaned, and pushed his vines into Ash's pussy and anus gently. Ash moaned around Bulbasaur's cock. He'd never taken it in both holes before, and even if it was just vines, the feeling was amazing. He began to take more of Bulbasaur's cock, bobbing his head along the length to push more and more of it down his throat.

Bulbasaur moaned loudly, pumping his vines deeper and deeper into Ash with every inch he took until Ash was deep-throating him and Bulbasaur was pushing his vines nine inches deep on both ends, trying to make Ash cum hard.

Even with Bulbasaur's efforts, he still came first, filling Ash's mouth with warm cum. Ash swirled the cum around in his mouth with his tongue, enjoying the earthy taste for a few moments before he swallowed it. Ash came another minute later, his holes tightening up around Bulbasaur's vines as he did so, groaning in pleasure at the release.

Bulbasaur withdrew his vines and stepped back from Ash, giving the next pokemon their turn. Charizard, impatient and annoyed at not getting to go first, refused to wait any longer. He came over as Ash was still getting up and grabbed his hips. Realizing what was happening, Ash stayed on his fours as Charizard thrust into him.

Ash yelped loudly, Charizard's cock being very big. He'd taken bigger of course thanks to Bruno, but it was still large. It didn't hurt as much as it would've though, and Ash was able to move his hips back to meet Charizard's while simply enjoying the pleasure of being taken roughly. Charizard groaned at the tightness of Ash's pussy, raising his hand and bringing it down hard on Ash's ass to give him even more pleasure.

Ash cried out at the smack, loving it. "K-keep going~!" Ash moaned, encouraging Charizard to thrust harder into him and smack his ass several times more. Ash came hard, clenching down around Charizard, but Charizard seemed to think Ash was getting tighter on purpose as a challenge. Th result was Charizard picking up the pace so much Ash's arms gave out, his face getting pressed against the ground as Charizard rammed into him harder and faster for several minutes before practically roaring as he came.

The cum completely filled Ash's cunt, and spilled out onto the ground. The sheer amount of it and the heat of it all pushed Ash into another climax., which thankfully helped to push some more of the Charizard cum out of him.

After this Ash needed a few minutes to rest, and Bulbasaur brought him an Oran berry to help him get his strength up. Once Ash was feeling energized again, he turned to the remaining pokemon, and beckoned his Quilava over. He grinned, and scampered over eagerly. Ash laid on his back, pulling Quilava on top of him to kiss him. Quilava's tongue was small, and Ash found it oddly pleasing to wrap his own tongue around it.

After several moments, they broke the kiss as Ask gestured for Quilava to pick a hole. He was small enough that he could reasonable use either without it hurting at all. Quilava chose Ash's pussy, lining and and pushing in gently. It felt good to go slowly after the roughness with Charizard, and Ash moaned as he held Quilava's head against his stomach, the smaller pokemon pumping his hips into his slick entrance slowly.

Quilava progressively picked up speed, his paws gripping Ash's sides for leverage as he went. He came into Ash after another ten minutes, his seed not scolding hot like Charizard's, just pleasantly warm.

Feeling a bit embarrassed about cumming before Ash did, Quilava moved back and began to eat Ash out to help him finish. He didn't seem to mind eating his own cum, and a bit of Charizard's, out of Ash's slit, and it was the sight of him doing so that made Ash finally cum more than the actual oral.

Quilava licked his face clean of cum, as well as Ash's inner thighs, and headed back to give the next pokemon their turn.

The next pokemon turned out to be a duo of Buizel and Infernape, who'd decided ahead of time to go together. Ash was surprised by this, but excited as Infernape picked him up. He was facing Buizel, who thrust his eight inches in hard as Infernape thrust into his ass from behind. Ash moaned loudly, enjoying how hard they pumped into him.

They were out of sync at first, but as they went, gradually started to work together, ramming into Ash in rhythm. Ash came long before they did, squeezing them both hard, but not making them cum for another five minutes; after which they still didn't stop, just turned Ash around and traded holes. Ash enjoyed the second position better, as Buizel's more slender member was able to push deeper into his ass while Infernape's thicker rod stretched out his pussy.

The feeling of extreme heat in one hole with a cooler dick filling the other was enough to make Ash cum again; this time making his two pokemon cum with him. Even after cumming in both holes, the two still weren't satisfied. They had Ash get to his knees between them, where he happily gripped their members and began stroking them both off.

He licked at the tip of one before switching to the other several times, always keeping them both aimed at his face. When they did finally cum, Buizel first followed by Infernape mere seconds after, their cum covered Ash's face, chest, and even got in his hair. Ash loved every second of it, and kept his mouth open through it all to catch as much as he could.

Ash used his hands to scoop up as much cum as he could to bring it to his mouth as Buizel and Infernape stepped back, letting Snivy step forward. Ash smiled as Snivy came forward. As good as it felt to be double teamed, he was getting sore, and was happy to have it gently again. What he didn't know was that Snivy had already decided that Ash would under no circumstances be getting it gently from her.

Her vines wrapped around his neck like a leash and pulled him down to his fours again, where Snivy placed her hands on his head and forced it against her pussy. Ash would've been lying if he'd said he wasn't getting a bit of a thrill from how dominant Snivy was, and he eagerly started eating her out. Snivy moaned softly, and moved her vines away from his neck to begin lashing his ass. Hard.

Ash yelped, only for Snivy to push his face back against her needy cunt. Ash was forced to keep eating while Snivy whipped his ass hard continuously with her vines. She only stopped when it felt like ass was getting close, at which point she paused long enough for Ash's climax to die back down for continuing to beat Ash's ass red.

It went on for almost half an hour, Snivy cumming four times and Ash not at all. Looking up, she beckoned another pokemon over while Ash couldn't see them, and used her vines to spread Ash's ass cheeks for them. Ash was about to get up as Snivy stepped back, onto to cry out in a mix of pleasure and pain when his Torterra rammed his unreasonably massive cock into Ash's tight asshole.

Ash couldn't even catch his breath to tell Torterra to ease up, which he would've in a heartbeat if he knew it was too much for Ash. Between Ash moaning loudly, most of which was his trying to speak getting garbled by the pain, and Snivy instructing him every few minutes that Ash wanted it even harder Torterra assumed Ash loved it, and kept going.

Following Snivy's words, he kept going harder and harder, fucking Ash's ass like it was a toy he was trying to break. Ash came hard, partly against his will, after twenty minutes of the savage fucking. Torterra himself didn't cum until nearly an hour later, filling Ash to the brim with cum. As Torterra pulled out, Snivy told him that Ash would really love it if he would fuck his throat just as hard.

Wanting Ash to feel as good as possible, Torterra quickly went over to Ash's face, ramming his cock into his down and down his throat the moment he tried to speak. Ash gagged, but Torterra pumped his hips to push even deeper. Ash could barely breath, but Snivy was getting off on his struggle, and Torterra was in bliss from how his throat squeezed around his cock.

It was another thirty minutes before Torterra came, nearly making Ash pass out. It took some effort, but Ash was able to swallow it all without choking. Afterwards Snivy had gone off somewhere else, and Torterra had left to.

Ash took a few minutes to rest before getting up on still shaky and slightly numb legs. 'Only one pokemon left,' Ash thought, not knowing what was coming. He figured he could just please Snorlax quickly, possibly even before he actually woke up, and then leave to get some rest. He didn't realize this wouldn't be the case until he saw the stampede coming towards him.

People often forgot that Ash had once captured fifty Tauros way back when **(Mostly because the episode was pulled in America)**. Even Ash had nearly forgotten this fact, until he saw all thirty rushing him down. He knew there was no point in running, si he stayed still and let it happen.

Over the course of the following two hours, every single square inch of Ash's body was re-purposed for pleasure. And not just by the males, who fucked his pussy, mouth, and ass two or three at a time, rubbed their cocks against his hands, feet, shoulders, and pretty much any unused piece of skin on him; the females seemed just as eager to essentially rape him. In fact, it was easier for the females to do so, as all they needed was a part of Ash to grind their pussy against and the force of their own powerful hips to grind against it.

Ash knew it would only hurt worse if he struggled, resisted, or thought too much about it, so he let his mind go blank, focusing only on the pleasure he got from being abused by so many pokemon at once, and just taking it all.

When it finally ended after two straight hours, Ash's stomach was extended so much from the mass amounts of cum in his stomach and ass that he looked eight months pregnant, not to mention being so coated in male and female cum that he had not a single doubt in his mind that he would be smelling like the stuff for a month.

Oddly though, as he laid their, trying to work the cum out of his body slowly and regain feeling in his legs and arms, he found that he didn't feel upset by what had happened. Sore as hell, yes, but he didn't mind that so much, and Bruno had left him feeling worse. Thinking on it, it probably would't have been too awful long before Ash had called them over himself to do this willingly.

That didn't mean he wasn't still going to use this event as an excuse to make Snivy into a submissive at some point, but that was more out of a personal curiosity for it than any actual bitterness.

After almost another hour, Ash finally managed to stand, most all of the cum out of his system. He started looking for his clothes so he could get dressed and go, only to be grabbed. He'd forgotten that Snorlax had been there the whole time, sleeping peacefully. Now he was awake, and he'd been promised sex. There wasn't a single chance Ash would be getting out of it.

Snorlax picked Ash up, and shifted so his pussy was right above his member. He recalled thinking Torterra's cock was unreasonable big. How ignorant he'd been only a few hours ago. Is Torterra's was unreasonably big, then Snorlax's was just plain logic defying. Ash wasn't so much positioned above it as he was sitting on it's tip, which was more than big enough to be used like a chair.

'There's no way it'll fit..' Ash thought to himself mere seconds before Snorlax forced him down with the same force he might've used to smash through concrete. Ash was proven very, very wrong as the massive cock forced it's way inside his pussy. There was no way he would every be taken anywhere near the full length, as he wasn't even halfway down and Snorlax had already bottomed out inside him, but that wouldn't stop Snorlax from trying very, very, VERY aggressively.

As Ash's mind started to fade for the time being, his eyes glazing over as Snorlax pulled him up and down by his hips, slowly stretching his body out even more as he used him like a living cock sleeve, Ash decided that, even if it wasn't always easy, being a cunt boy was always, _always,_ interesting. And he wouldn't trade it for anything.

Even if he did end up getting fucked into unconsciousness by a Snorlax who kept fucking him for hours more afterwards, leaving him to wake up so full of cum that A: he felt ready to burst, and B: the smell attracted some very rapey looking wild pokemon.

* * *

 **And that's a wrap! I'll be honest, I was pretty sure this would be the story that got me kicked off of FF net, and I'm so thankful you all liked it. Let me know what character you'd like to see getting fucked as a Cunt Boy!**

 **I am sinful by nature with no malicious intent, and I'll see you all next time!**


End file.
